Structure and stereochemistry of lapiferin

Golovina, L. A.; Saidkhodzhaev, Ashraf I.; Абдуллаев, Н. Д.; Malikov, V. M.; Yagudaev, M. R.

doi:10.1007/bf00579759

Cited by 6 publications

(8 citation statements)

References 3 publications

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“…Five oxygen bearing carbons were assigned at C 85.4 (C-4), 69.1 (C-6), 56.1 (C-8), 59.7 (C-9) and 71.5 (C-10) (Diaz et al, 1984;Golovina et al, 1983). Other proton and carbon signals were determined by HMQC and HMBC.…”

Section: Resultsmentioning

confidence: 99%

“…In an earlier report, lapiferin was purified from the roots of F. lapidosa and its structure and configuration have been established on the basis of chemical transformations and the analysis of spectral characteristics (Diaz, Fragam, Gonzala`z, Gonzala`z, & Hernandez, 1984;Golovina, Saidkhodzhaev, Abdullaev, Malikov, & Yagudaev, 1983). Recently, lapiferin extracted from F. communis and F. arrigonii sardinian showed antiproliferative activity against human colon cancer, and the interaction with type II estrogen-binding sites underlies this activity (Poli et al, 2005).…”

Section: Introductionmentioning

confidence: 98%

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A crystal lapiferin derived from Ferula vesceritensis induces apoptosis pathway in MCF-7 breast cancer cells

Gamal‐Eldeen¹,

Hegazy

2010

Natural Product Research

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Ferula vesceritensis is a plant that is used in the traditional medicine in Algeria. Chromatographic investigation of the methylene chloride/methanol extract of the aerial parts of F. vesceritensis afforded a crystal carotene sesquiterpene designed lapiferin (10alpha-acetoxy-6alpha-angeloyloxy-8alpha,9alpha-epoxy-trans-caxotan-4beta-ol) for the first time from this species. The structure was determined by comprehensive NMR studies, including DEPT, COSY, NOE, HMQC, HMBC and HRMS, and X-ray data of lapiferin. We report here for the first time the isolation of lapiferin from F. vesceritensis as a new natural source, and we additionally report the first X-ray data for lapiferin. We also report for the first time the specific anti-cancer activity of lapiferin against human breast cancer cells (MCF-7), which is due to apoptosis and not necrosis. Moreover, we have identified for the first time the cell death pathway induced by lapiferin in human breast cancer cells, and also that lapiferin evokes multiple consequences that trigger apoptotic cell death, involving the enhancement of DNA fragmentation, the activation of caspases and the induction of histone acetylation in MCF-7 cells. In conclusion, we record here F. vesceritensis as a new natural source of lapiferin and its first X-ray analysis, and the promising specific anti-cancer activity against human breast cancer of lapiferin and accordingly F. vesceritensis extract.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

A crystal lapiferin derived from Ferula vesceritensis induces apoptosis pathway in MCF-7 breast cancer cells

Gamal‐Eldeen¹,

Hegazy

2010

Natural Product Research

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“…Lapiferin is a complex ester of sesquiterpene alcohols with aliphatic acid, which does not possess ionophoric properties ( 28 ). Earlier studies have purified lapiferin from the roots of F. lapidosa , and established its structure and configuration based on chemical transformations and analysis of spectral characteristics ( 29 , 30 ). In addition, lapiferin extracted from F. communis and F. arrigoniisardinian has been shown to exert anti-proliferative activity against human colon cancer via interactions with type II estrogen-binding sites ( 20 ).…”

Section: Discussionmentioning

confidence: 99%

The natural product lapiferin inhibits cell proliferation and promotes cell apoptosis in gingival squamous cell carcinoma via P21 regulation

et al. 2021

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“…Among the therapeutic TCMs, lapiferin is a novel agent that is a complex ester of sesquiterpene alcohols with aliphatic acid and does not possess ionophoric properties (13). Lapiferin is extracted from the roots of F. lapidosa and its structure and configuration have been established based on chemical transformation and analysis of spectral characteristics (14). The crystal data of lapiferin is as follows: C 22 H 34 O 6 , mol.…”

Section: Introductionmentioning

confidence: 99%

Lapiferin protects against H1N1 virus-induced pulmonary inflammation by negatively regulating NF-kB signaling

Pei

Gao²,

et al. 2020

Braz J Med Biol Res

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H1N1 virus-induced excessive inflammatory response contributes to severe disease and high mortality rates. There is currently no effective strategy against virus infection in lung. The present study evaluated the protective roles of a natural compound, lapiferin, in H1N1 virus-induced pulmonary inflammation in mice and in cultured human bronchial epithelial cells. Initially, Balb/C mice were grouped as Control, H1N1 infection (intranasally infected with 500 plaque-forming units of H1N1 virus), lapiferin (10 mg/kg), and H1N1+lapiferin (n=10/group). Lung histology, expression of inflammatory factors, and survival rates were assessed after 14 days of exposure. Administration of lapiferin significantly alleviated the virus-induced inflammatory infiltrate in lung tissues. Major pro-inflammatory cytokines, such as interleukin (IL)-1b, IL-6, and tumor necrosis factor (TNF)-a, were decreased at both mRNA and protein levels by lapiferin administration in the lung homogenate. Lapiferin also reduced inflammatory cell numbers in bronchoalveolar fluid. Mechanistically, lapiferin suppressed the transcriptional activity and protein expression of NF-kB p65, causing inhibition on NF-kB signaling. Pre-incubation of human bronchial epithelial cells with an NF-kB signaling specific activator, ceruletide, significantly blunted lapiferin-mediated inhibition of pro-inflammatory cytokines secretion in an air-liquid-interface cell culture experiment. Activation of NF-kB signaling also blunted lapiferin-ameliorated inflammatory infiltrate in lungs. These results suggested that lapiferin was a potent natural compound that served as a therapeutic agent for virus infection in the lung.

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Structure and stereochemistry of lapiferin

Cited by 6 publications

References 3 publications

A crystal lapiferin derived from Ferula vesceritensis induces apoptosis pathway in MCF-7 breast cancer cells

A crystal lapiferin derived from Ferula vesceritensis induces apoptosis pathway in MCF-7 breast cancer cells

The natural product lapiferin inhibits cell proliferation and promotes cell apoptosis in gingival squamous cell carcinoma via P21 regulation

Lapiferin protects against H1N1 virus-induced pulmonary inflammation by negatively regulating NF-kB signaling

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